The most obvious answer of what to do in Aspen in the winter is to ski but for those winter visitors that do not ski or just need a day off from the slopes there are plenty of other options.
Top things to do in Aspen during the winter
#1 Take a Tour. Dean’s Aspen Tours, of course, is a great activity in the winter. Fun, casual and informative. Just a great way to connect with Aspen, Colorado.
#2 Play in the snow. Snow sledding is great for all ages. One of the most popular sledding hills is behind the Aspen Recreation Center. It is wide, long and fairly steep. It can be a blast. Sleds are rented at the recreation center or often loaned from hotels/airbnbs/condos. Do proceed with caution. The sled hill is pretty clear of obstacles other than a few small jumps, avoid these, and other sledders, so wait till the run is clear when descending and stay off to the side when walking back up.
#3 Art Walk. Tap into the art galleries, sculptures & street art on a walk through downtown Aspen. The Aspen Art Museum in downtown Aspen is a free admission museum and a great way to spend an hour.
#4 Shopping. Window shop high end luxury brands that dominate the downtown core as well as some funky shops and souvenir shops.
What not to do in Aspen in the winter?
Expect to see the Maroon Bells. Viewed from a distance from the top of Highlands ski mountain is probably your best bet for viewing the Maroon Bells in the winter as the access road is closed, with a locked gate and not plowed of snow. There is a chance to visit via snowmobile tour when avalanche danger is low but your best bet is to visit the Maroon Bells in the Spring, Summer & Fall.